WO2017213855A1 - Revêtement à base d'amide - Google Patents

Revêtement à base d'amide Download PDF

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Publication number
WO2017213855A1
WO2017213855A1 PCT/US2017/034275 US2017034275W WO2017213855A1 WO 2017213855 A1 WO2017213855 A1 WO 2017213855A1 US 2017034275 W US2017034275 W US 2017034275W WO 2017213855 A1 WO2017213855 A1 WO 2017213855A1
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WIPO (PCT)
Prior art keywords
isocyanate
coating
proppant
coated article
carboxylic acid
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Application number
PCT/US2017/034275
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English (en)
Inventor
Arjun RAGHURAMAN
Sachit GOYAL
Phillip S. Athey
Harshad M. Shah
Juan Carlos Medina
William A. Koonce
Original Assignee
Dow Global Technologies Llc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by Dow Global Technologies Llc filed Critical Dow Global Technologies Llc
Priority to BR112018075389A priority Critical patent/BR112018075389A2/pt
Priority to CA3027004A priority patent/CA3027004A1/fr
Priority to CN201780035150.8A priority patent/CN109348721A/zh
Publication of WO2017213855A1 publication Critical patent/WO2017213855A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/60—Compositions for stimulating production by acting on the underground formation
    • C09K8/80—Compositions for reinforcing fractures, e.g. compositions of proppants used to keep the fractures open
    • C09K8/805—Coated proppants

Definitions

  • Embodiments relate to amide based coatings for articles (such as proppants) articles that have the amide based coatings thereon, methods of making the amide based coatings, and methods of coating the articles with the amide based coatings.
  • Polymeric protective coatings (which include set in place coatings, spray coatings, powder coatings, and paints) may be used to protect metal and concrete substrates from corrosion by providing a barrier between a corrosive environment and a substrate.
  • the protective coatings may be designed to minimize the permeation through the polymer of corrosive species commonly found in aqueous or organic media. It is proposed that the protective coating may enable recovery of materials such as heavy metals and/or sulfides. Accordingly, it is proposed to develop coating technologies for enabling such recovery.
  • well fracturing is a process of injecting a fracturing fluid at high pressure into subterranean formations such as subterranean rocks, well holes, etc., so as to force open existing fissures and extract a crude product such as oil or gas therefrom.
  • Proppants are solid material in particulate form for use in well fracturing. Proppants should be strong enough to keep fractures propped open in deep hydrocarbon formations, e.g., during or following an (induced) hydraulic fracturing treatment. Thus, the proppants act as a "propping agent" during well fracturing.
  • the proppants may be introduced into the subterranean formations within the fracturing fluid.
  • the proppants may be coated for providing enhanced properties such as hardness and/or crush resistance. It is further desired to find coatings that provide further improved proppant flowback control.
  • Proppant flowback refers to dislodging of proppants followed by transport up a well hole with the flowback water. Such proppant flowback may occur, e.g., during well cleanup or after well completion, and may lead to undersirable deposits (such as in casings) and/or failure of electrical submersible pumps. Further, proppant flowback may negatively impact proppant pack conductivity and/or result in pinching off the well hole. Therefore, there is a need for cost-effective technologies to reduce, minimize, and/or prevent such proppant flowback, while not negatively impacting proppant handling (e.g., remain substantially free-flowing during storage and transportation).
  • a proposed method is to a polymeric coating formatted from a bond only under the high temperature conditions in the subterranean formations.
  • high temperature activated polymeric coating can only be used in subterranean formations that meet the specific requirements for activation of the coating, otherelse a higher amount of proppant flowback may be realized. Accordingly, it is proposed to develop flowback control technologies that are usable in relatively lower temperature subterranean formations, while retaining handling characteristics.
  • Embodiments may be realized by providing a coated article that comprises an article, and one or more amide based coatings on an outer surface of the proppant particle, the amide based coating include the reaction product of an isocyanate component that includes at least one isocyanate and a carboxylic acid component that includes one or more poly-carboxylic acids.
  • FIG. 1 illustrates SEM analysis at 10.0 kV of ten different samples of coated sand with scale bars, as indicated.
  • an amide based coating is derived from the reaction between a carboxylic acid and an isocyanate, which results in an amide bond and CO2 gas.
  • a carboxylic acid and an isocyanate results in an amide bond and CO2 gas.
  • embodiments relate to proppant coatings that are formed from the reaction of a polycarboxylic acid and a polyisocyanate.
  • Such resin coated proppants out of these compositions may display sufficient bond strength at temperatures as low as 50 °C.
  • such coatings may be utilized to capture contaminates such as 100% of 3 ⁇ 4S from aqueous media containing.
  • the amide based coating may be an amide copolymer coating.
  • the amide based coating may be derived from the reaction between a carboxylic acid and an isocyanate, which results in an amide bond and CO2 gas.
  • the amine bond forming reaction is as shown in the Schematic below.
  • Schematic (a) illustrates the reaction between a carboxylic acid and an isocyanate.
  • Schematic (b) illustrates an exemplary route that may be used used to prepare pre-cured resin coated proppants according to an exemplary embodiment that utilizes the reaction between a carboxylic acid and an isocyanate.
  • the amide based coating may be prepared using a carboxylic acid based copolymer that is prepared using one or more polyols, such as a polyester, polycarbonate, and/or polyether polyol.
  • a carboxylic acid based copolymer that is prepared using one or more polyols, such as a polyester, polycarbonate, and/or polyether polyol.
  • Schematic (a) illustrates an exemplary route that may be used to prepare to synthesize of acid terminated polyethers.
  • Schematic (b) illustrates an exemplary route that may be used to prepare the reaction of acid- terminated polyether with isocyanate to generate an amide based coating.
  • the coated article may include one of more coatings that allow for dual function coating that provide the benefit of controlled release of an additive and/or capture of containments.
  • the one or more coatings may comprise from 0.5 wt% to 10.0 wt% (e.g., 0.5 wt% to 5.0 wt%, 0.5 wt% to 4.0 wt%, 0.5 wt% to 3.5 wt%, etc.) of a total weight of the coating article.
  • coated articles such as proppants include an underlying coating formed on a core (e.g., directly on so as to encompass and/or substantially encompass).
  • the core may be a proppant core, such as sand.
  • the coated article includes at least one amide based coating.
  • embodiment (a) includes an underlying additive based coating (e.g., including at least one well treatment agent) coated on an outer surface of an article such as a proppant sand particle and an overlying polymer resin based coating coated on the underlying additive based coating.
  • Embodiment (b) includes a single coating that is based on both an additive and the polymer resin.
  • the additive may be dispersed in the polymer resin matrix.
  • the additive may be chemically linked to the polymer resin.
  • the underlying additive based coating may be directly on an outermost surface of the article (such as proppant particle) and the overlying polymer resin based coating may be directly on the underlying additive based coating, opposing the outermost surface of the article.
  • the overlying polymer resin based coating may form an outermost surface of the coated article, with the underlying additive based coating directly under the overlying polymer resin based coating, such that other coatings may be between the outermost surface of the article and the underlying additive based coating.
  • the single coating may be directly on an outermost surface of the article (such as proppant particle) and/or may form an outermost surface of the coated article.
  • the coated article may provide the benefit of being formulated to maintain its properties even when exposed to relatively low temperatures for down well applications, e.g., to temperatures of near 50°C and/or less than 70°C.
  • performance of coatings for proppants may be further improved by designing a multilayer coating structure, which may include one layer that may be permeable or semi-permeable and another layer composed of polymer resin matrix that can retain a high storage modulus at high temperatures.
  • the proppant article may be coated with additional coatings and/or additional additives, such as additives for recovery and/or removal of other contaminates.
  • the amide based coating may be formed on a pre-formed polymer resin coated article (such as a proppant) or may be formed immediately after and/or concurrent with forming the amide coated article.
  • the amide based coating may be applied to various articles that include the proppant and/or other base substrates.
  • the amide based coating may act as a permeable polymer resin, with respect to the one or more additives.
  • the amide based coating may enable capturing of containments, such as heavy metals and/or sulfides.
  • the amide based coating may enable delayed released of a majority amount of the one or more additives embedded there within.
  • At least one additive may be rendered immobile on an outer surface of the proppant particle and/or rendered immobile within the amide based polymer matrix, but as over a period of time the additive may be released/move through the polymer resin coating, so as to be released into the surrounding environment (e.g., into a fracturing fluid).
  • the amide based coating which may be a coating on (e.g., directly on) an outer surface of an article such as a proppant particle.
  • the coated article such as the proppant particle may optional include additional coats/layers, such as on or under the amide based coating.
  • the amide based coating may include at least additive embedded on and/or within a polymer resin matrix. The one or more additives may be added during a process of forming the amide based coating and/or may be sprinkled onto a previously coated solid core proppant particle to form the amide based coating in combination with an additive based coating.
  • the one or more additives may be incorporated into an isocyanate-reactive component for forming the amide based coating, an isocyanate component (e.g., a polyisocyanate and/or a prepolymer derived from an isocyanate and a prepolymer formation isocyanate-reactive component) for forming the amide based coating, the prepolymer formation isocyanate-reactive component, and/or a prepolymer derived from an isocyanate and a one component system formation isocyanate-reactive component.
  • an isocyanate component e.g., a polyisocyanate and/or a prepolymer derived from an isocyanate and a prepolymer formation isocyanate-reactive component
  • the one or more additives may be provided in a carrier polymer when forming controlled release polymer resin based coating.
  • exemplary carrier polymers include simple polyols, polyether polyols, polyester polyols, liquid epoxy resin, liquid acrylic resins, polyacids such as polyacrylic acid, a polystyrene based copolymer resins (exemplary polystyrene based copolymer resins include crosslinked polystyrene-divinylbenzene copolymer resins), Novolac resins made from phenol and formaldehyde (exemplary Novolac resins have a low softening point), and
  • additives include moisture scavengers, UV stabilizers, demolding agents, antifoaming agents, blowing agents, adhesion promoters, curatives, pH neutralizers, plasticizers, compatibilizers, flame retardants, flame suppressing agents, smoke suppressing agents, and/or pigments/dyes.
  • the polymer resin/matrix is the reaction product of an isocyanate component and an isocyanate-reactive component that includes (e.g., consistent essentially of) one or more carboxylic acids (e.g., one or more polycarboxylic acids).
  • the isocyanate component may include at least one polyisocyanate and/or at least one isocyanate-terminated prepolymer and the isocyanate-reactive component may include at least one polyol such as a polyether polyol.
  • an optional one or more amide based undercoats may be the reaction product of a same or a different isocyanate component and a same or a different isocyanate-reactive component.
  • the optional one or more amide based undercoats may include one or more additives, such that the underlying layer includes a amide resin based matrix.
  • a single isocyanate component may be used to form both an amide based undercoat and a separately formed amide based matrix.
  • one isocyanate-reactive component and one isocyanate component may be used to form the amide based undercoat and additional isocyanate- reactive and isocyanate components may be used to form the overlaying amide based coating.
  • the mixture for forming the polyurethane based matrix may have an isocyanate index that is at least 60 (e.g., at least 100).
  • the isocyanate index may be from 60 to 2000 (e.g., 65 to 1000, 65 to 300, 65 to 250, 70 to 200, 100 to 900, 100 to 500, etc.)
  • the isocyanate index is the ratio of the isocyanate groups over the isocyanate reactive hydrogen atoms from a carboxylic acid present in a formulation, given as a percentage.
  • the isocyanate index expresses the percentage of isocyanate actually used in a formulation with respect to the amount of isocyanate theoretically required for reacting with the amount of isocyanate-reactive hydrogen used in a formulation.
  • the isocyanate component for forming the polyurethane resin (including a polyurethane/epoxy hybrid based matrix) and/or the polyurethane based undercoat may include one or more polyisocyanates, one or more isocyanate-terminated prepolymer derived from the polyisocyanates, and/or one or more quasi-prepolymers derived from the polyisocyanates.
  • Isocyanate-teiminated prepolymers and quasi-prepolymers may be prepared by reacting a stoichiometric excess of a polyisocyanate with at least one polyol.
  • Exemplary polyisocyanates include aromatic, aliphatic, and cycloaliphatic
  • the isocyanate component may only include aromatic polyisocyanates, prepolymers derived therefrom, and/or quasi-prepolymers derived therefrom, and the isocyanate component may exclude any aliphatic isocyanates and any cycloaliphatic polyisocyanates.
  • the polyisocyanates may have an average isocyanate functionality from 1.9 to 4 (e.g., 2.0 to 3.5, 2.8 to 3.2, etc.).
  • the polyisocyanates may have an average isocyanate equivalent weight from 80 to 160 (e.g., 120 to 150, 125 to 145, etc.)
  • the isocyanate-terminated prepolymer may have a free NCO (isocyanate moiety) of 10 wt% to 35 wt%, 10 wt% to 30 wt%, 10 wt% to 25 wt%, 10 wt% to 20 wt%, 12 wt% to 17 wt%, etc.
  • Exemplary isocyanates include toluene diisocyanate (TDI) and variations thereof known to one of ordinary skill in the art, and diphenylmethane diisocyanate (MDI) and variations thereof known to one of ordinary skill in the art.
  • Other isocyanates known in the polyurethane art may be used, e.g., known in the art for polyurethane based coatings. Examples, include modified isocyanates, such as derivatives that contain biuret, urea, carbodiimide, allophonate and/or isocyanurate groups may also be used.
  • Exemplary available isocyanate based products include PAPITM products, ISONATETM products and VORANATETM products,
  • the isocyanate-reactive component for forming the amide based coating includes one or more carboxylic acids, e.g., one or more poly-carboxylic acids.
  • the isocyanate-reactive component may include one or more poly-carboxylic acids (such as a simple carboxylic acid and/or a poly-carboxylic acid copolymer) that has a number average molecular weight from 90 g/mol to 10,000 g/mol.
  • the one or more poly-carboxylic acids may include one or more simple poly-carboxylic acids (also referred to as a poly-carboxylic acid monomers) such as a dicarboxylic acid and a tricarboxylic acid such as citric acid.
  • the dicarboxylic acid may have the general formula H0 2 C(CH2)nC0 2 H.
  • the one or more poly-carboxylic acids may include one or more poly-carboxylic acid copolymers that include two or more carboxylic acid end groups and a polymer backbone.
  • the carboxylic acid end groups may be referred to as a measure of the nominal carboxylic acid functionality of the copolymer.
  • the nominal carboxylic acid functionality may be from 2 to 8 (e.g., 2 to 6, 2 to 5, 2 to 4, and/or 2 to 3).
  • the backbone may be an ether, ester, and/or carbonate based backbone. The ether, ester, and/or carbonate backbone may be non- reactive with the isocyanate-component.
  • the ether backbone may be a polyether derived from reaction of propylene oxide, ethylene oxide, and/or butylene oxide with an initiator.
  • the ether backbone may have a number average molecular weight from 60 g/mol to less than 9950 g/mol.
  • the poly carboxylic acid copolymer may be the reaction product of one or more polyether polyols and one or more anhydrides.
  • the poly carboxylic acid can be derived from polyether polyols by direct oxidation of alcohol end groups.
  • the one or more poly-carboxylic acids may be pre-made as a blend prior to forming the amide based coating.
  • at least one poly-carboxylic acid copolymer and at least one poly-carboxylic acid monomer may be blended and maintained at a high temperature, such as at least 80°C) over an extended period of time (such as at least 2 hours) to form the pre-made blend.
  • the isocyanate-reactive component for forming the polyurethane resin and/or the polyurethane based undercoat may further include a catalyst component that includes one or more catalysts.
  • Catalysts known in the art such as trimerization catalysts known in art for forming polyisocyanates trimers and/or urethane catalyst known in the art for forming polyurethane polymers and/or coatings may be used.
  • the catalyst component may be pre-blended with the isocyanate-reactive component, prior to forming a coating.
  • trimerization catalysts include, e.g., amines (such as tertiary amines), alkali metal phenolates, alkali metal alkoxides, alkali metal carboxylates, and quaternary ammonium carboxylate salts.
  • the trimerization catalyst may be present, e.g., in an amount less than 5 wt%, based on the total weight of the isocyanate-reactive component.
  • Exemplary urethane catalyst include various amines, tin containing catalysts (such as tin carboxylates and organotin compounds), tertiary phosphines, various metal chelates, and metal salts of strong acids (such as ferric chloride, stannic chloride, stannous chloride, antimony trichloride, bismuth nitrate, and bismuth chloride).
  • Exemplary tin-containing catalysts include, e.g., stannous octoate, dibutyl tin diacetate, dibutyl tin dilaurate, dibutyl tin dimercaptide, dialkyl tin dialkylmercapto acids, and dibutyl tin oxide.
  • the urethane catalyst when present, may be present in similar amounts as the trimerization catalyst, e.g., in an amount less than 5 wt%, based on the total weight of the isocyanate-reactive component.
  • the amount of the trimerization catalyst may be greater than the amount of the urethane catalyst.
  • the catalyst component may include an amine based trimerization catalyst and a tin-based urethane catalyst.
  • exemplary catalyst include amide forming catalysts that are known in the art, such as N-methyl imidazole and Lewis bases.
  • the coated particle may include additional coatings in addition to the additive based coating and the controlled released polymer resin based coating.
  • a total amount of all the optional coatings may be from 0.5 wt% to 7.0 wt% (e.g., 1.0 wt% to 4.0 wt%, 1.0 wt% to 3.5 wt%, 1.5 wt% to 3.0 wt%, 2.0 wt% to 3.0 wt%, etc.), based on the total weight of the coated article such as coated proppant.
  • a controlled release polymer resin based coating such as discussed in U.S. Provisional Patent Application No. 62/312,113, which may be the top coat (outermost coating) forming the coated article such as proppant particle.
  • the controlled released polymer resin based coating includes one or more well treatment agents that are embedded in a polymer resin matrix, the matrix may include the amide based material described above and/or a polyurethane resin, epoxy resin, phenolic resin, and/or furan resin.
  • Exemplary well treatment agents are described as follows: (1) With respect to scale inhibitor, it is meant a chemical additive that acts to reduce the rate of and/or prevent the precipitation and aggregation of slightly insoluble formations on the walls of systems, e.g., systems used in a well fracturing process. (2) With respect to wax inhibitor, it is meant a chemical additive that acts to reduce the rate of and/or prevent the precipitation out of wax and/or paraffin from a fluid, e.g., the wax and/or paraffin may be a natural compound found in the crude product obtained during a well fracturing process.
  • pour point depressant it is meant a chemical additive that lowers the pour point of a crude product obtained during a well fracturing process, whereas the pour point is the lowest temperature at which the product will pour when cooled under defined conditions and may be indicative of the amount of wax in the product (at low temperatures the wax may separate, inhibiting flow).
  • asphaltene inhibitor it is meant a chemical additive that acts to reduce the rate of and/or prevent the precipitation out of asphaltene (such as destabilized asphaltene), e.g., whereas asphaltene molecules may be found in the crude product obtained during a well fracturing process.
  • asphaltene dispersant it is meant a chemical additive that acts to increase the fluidity of the crude product that includes precipitated asphaltene, e.g., whereas asphaltene molecules may be found in the crude product obtained during a well fracturing process.
  • corrosion inhibitor it is meant a chemical additive that acts to reduce the rate of and/or prevent corrosive effect of acids on metals and/or metal alloy based components used in systems, e.g., systems used in a well fracturing process.
  • biocide also referred to as a disinfectant
  • a chemical additive that acts to reduce the rate of and/or prevent the growth of bacteria/microbes in the well, which bacteria may interfere with a process, e.g., a well fracturing process.
  • viscosity modifier also referred to as a viscosity improver
  • a chemical additive that is sensitive to temperature, e.g., such that at low temperatures, the molecule chain contracts and does not impact the fluid viscosity and at high temperatures the molecule chain relaxes and an increase in viscosity occurs.
  • de-emulsifier also referred to as emulsion preventers
  • emulsion preventers it is meant a chemical additive that reduces and/or minimizes interfacial tensions within the crude product obtained during a well fracturing process.
  • the de-emulsifier may lower the shear viscosity and the dynamic tension gradient of an oil- water interface in the crude product.
  • a heavy metal recovery coating such as discussed in priority document, U.S. Provisional Patent Application No. 62/186,645 and/or a sulfide recovery coating such as discussed in priority document, U.S. Provisional Patent Application No. 62/287,037 may be included.
  • the heavy metal recovery coating may have heavy metal recovery crystals embedded within a polymer resin matrix, which is coated onto a solid core proppant particle.
  • the metal sulfate crystals on the proppant particle may aid in heavy metal recovery by causing heavy metals, such as particles of radioactive radium, to partition onto the coated proppant and away from the contaminated water.
  • heavy metals such as particles of radioactive radium
  • the selective post-precipitation of heavy metals such radium ions onto previously formed crystals (e.g., barite crystals) by lattice replacement (lattice defect occupation), adsorption, or other mechanism, is distinctly different from other capture modes such as ion exchange or molecular sieving.
  • the post precipitation of heavy metals such as radium on pre-formed barite crystals is selective for radium because of similar size and electronic structure of radium and barium.
  • the heavy metal recovery crystals may form a crystalline structure that is appropriately sized to hold the heavy metals such as radium thereon or therewithin. Therefore, the heavy metal recovery crystals may pull the radium out of fracturing fluid and hold the ions on or within the heavy metal recovery coating, so as to reduce radium content in the fracturing fluid.
  • the sulfide recovery coating may provide a system in which sulfides such as hydrogen sulfide may be removed from contaminated water, e.g., can be absorbed into/onto a matrix and/or may be chemically altered.
  • the sulfide may be chemically altered to form sulfur dioxide.
  • the sulfide capturing agent may be embedded within a polymer resin matrix, which is coated onto a proppant particle, such that optionally the sides of the sulfide capturing agent are encapsulated by the polymer resin.
  • the sulfide capturing agent on the proppant particle may aid in the recovery and/or removal of sulfides from the contaminated water.
  • the sulfide capturing agents are solids at room temperature (approximately 23 °C).
  • the sulfide capturing crystals may have a melting point greater than 500 °C, greater than 800 °C, and/or greater than 1000 °C.
  • the sulfide capturing agents such as the sulfide capturing crystals, may have an average particle size of less than 5 ⁇ (e.g., less than 4 ⁇ , less than 2 ⁇ , less than 1 ⁇ , etc.)
  • the polymer resin matrix having the sulfide capturing agent may act as a permeable or semi-permeable polymer resin, with respect to hydrogen sulfide and/or sulfur ions.
  • the hydrogen sulfide and/or sulfur ions may be rendered immobile on an outer surface of the proppant particle and/or rendered immobile within the polymer resin matrix.
  • the polymer resin matrix, polymer coating, and/or the process used to prepare coated proppants may be designed to retain captured sulfide on or within the coatings of the proppants and keep the product in the fracture.
  • the sulfide recovery coating may include both the sulfide capturing agent and the heavy metal recovery crystals embedded within a same polymer resin matrix, to form both the sulfide recovery coating and the heavy mental recovery coating.
  • the additional layer is derived from a mixture that includes one or more preformed isocyanurate tri- isocyanates and one or more curatives.
  • the preformed isocyanurate tri-isocyanate may also be referred to herein as an isocyanate trimer and/or isocyanurate trimer.
  • the isocyanurate tri-isocyanate is prepared prior to making a coating that includes the isocyanurate tri-isocyanate there within. Accordingly, the isocyanurate tri-isocyanate is not prepared via in situ trimerization during formation of the coating.
  • one way of preparing polyisocyanates trimers is by achieving in situ trimerization of isocyanate groups, in the presence of suitable trimerization catalyst, during a process of forming polyurethane polymers.
  • the in situ trimerization may proceed as shown below with respect to Schematic (a), in which a diisocyanate is reacted with a diol (by way of example only) in the presence of both a urethane catalyst and a trimerization (i.e. promotes formation of isocyanurate moieties from isocyanate functional groups) catalyst.
  • the resultant polymer includes both polyurethane polymers and polyisocyanurate polymers, as shown in Schematic (a), below.
  • the preformed isocyanurate tri-isocyanate is provided as a separate preformed isocyanurate-isocyanate component, i.e., is not mainly formed in situ during the process of forming
  • the preformed isocyanurate tri-isocyanate may be provided in a mixture for forming the coating in the form of a monomer, and not in the form of being derivable from a polyisocyanate monomer while forming the coating.
  • the isocyanate trimer may not be formed in the presence of any polyols and/or may be formed in the presence of a sufficiently low amount of polyols such that a polyurethane forming reaction is mainly avoided (as would be understand by a person of ordinary skill in the art).
  • the preformed isocyanurate tri-isocyanate it is believed that the existence of isocyanurate rings leads to a higher crosslink density.
  • the higher crosslink density may be coupled with a high decomposition temperature of the isocyanurate rings, which may lead to enhanced temperature resistance. Accordingly, it is proposed to introduce a high level of isocyanurate rings in the coatings for proppants using the preformed isocyanurate tri-isocyanates.
  • the additional layer may include one or more preformed aliphatic isocyanate based isocyanurate tri-isocyanates, one or more preformed cycloaliphatic isocyanate based isocyanurate tri-isocyanates, or combinations thereof.
  • the additional layer is derived from at least a preformed cycloaliphatic isocyanate based isocyanurate tri-isocyanate, e.g., the preformed cycloaliphatic isocyanate based isocyanurate tri-isocyanate may be present in an amount from 80 wt% to 100 wt%, based on the total amount of the isocyanurate tri- isocyanates used in forming the additional layer.
  • Exemplary preformed isocyanurate tri-isocyanates include the isocyanurate tri-isocyanate derivative of 1 ,6-hexamethylene diisocyanate (HDI) and the isocyanurate tri-isocyanate derivative of isophorone diisocyanate (IPDI).
  • the isocyanurate tri-isocyanates may include an aliphatic isocyanate based isocyanurate tri- isocyanates based on HDI trimer and/or cycloaliphatic isocyanate based isocyanurate tri-isocyanates based on IPDI trimer.
  • the one or more curatives may include an amine based curative such as a polyamine and/or an hydroxyl based curative such as a polyol.
  • the one or more curatives may include one or more polyols, one or more polyamines, or a combination thereof.
  • Curative known in the art for use in forming coatings may be used.
  • the curative may be added, after first coating the proppant with the preformed aliphatic or cycloaliphatic isocyanurate tri-isocyanate.
  • the curative may act as a curing agent for both the top coat and the undercoat.
  • the curative may also be added, after first coating following the addition of the preformed aliphatic or cycloaliphatic isocyanurate tri-isocyanate in the top coat.
  • Various optional ingredients may be included in the reaction mixture for forming the controlled release polymer resin based coating, the additive based coating, and/or the above discussed additional coating/layer.
  • reinforcing agents such as fibers and flakes that have an aspect ratio (ratio of largest to smallest orthogonal dimension) of at least 5 may be used.
  • These fibers and flakes may be, e.g., an inorganic material such as glass, mica, other ceramic fibers and flakes, carbon fibers, organic polymer fibers that are non-melting and thermally stable at the temperatures encountered in the end use application.
  • Another optional ingredient is a low aspect ratio particulate filler, that is separate from the proppant.
  • Such a filler may be, e.g., clay, other minerals, or an organic polymer that is non-melting and thermally stable at the temperatures encountered in stages (a) and (b) of the process.
  • a particulate filler may have a particle size (as measured by sieving methods) of less than 100 ⁇ .
  • the undercoat may be formed using less than 20 wt % of solvents, based on the total weight of the isocyanate -reactive component.
  • Exemplary proppants include silica sand proppants and ceramic based proppants (for instance, aluminum oxide, silicon dioxide, titanium dioxide, zinc oxide, zirconium dioxide, cerium dioxide, manganese dioxide, iron oxide, calcium oxide, and/or bauxite).
  • ceramic based proppants for instance, aluminum oxide, silicon dioxide, titanium dioxide, zinc oxide, zirconium dioxide, cerium dioxide, manganese dioxide, iron oxide, calcium oxide, and/or bauxite.
  • Various other exemplary proppant material types are mentioned in literature, such as glass beads, walnut hulls, and metal shot in, e.g., Application Publication No. WO 2013/059793, and polymer based proppants as mentioned by U.S. Patent Publication No. 2011/0118155.
  • the sand and/or ceramic proppants may be coated with a resin to, e.g.
  • the proppants to be coated may have an average particle size from 50 ⁇ to 3000 ⁇ (e.g., 100 ⁇ to 2000 ⁇ ).
  • Proppant particle (grain or bead) size may be related to proppant performance.
  • Particle size may be measured in mesh size ranges, e.g., defined as a size range in which 90% of the proppant fall within.
  • the proppant is sand that has a mesh size of 20/40.
  • Lower mesh size numbers correspond to relatively coarser (larger) particle sizes.
  • Coarser proppants may allow higher flow capacity based on higher mesh permeability. However, coarser particles may break down or crush more readily under stress, e.g., based on fewer particle-to-particle contact points able to distribute the load throughout the mesh. Accordingly, coated proppants are proposed to enhance the properties of the proppant particle.
  • the performance of coatings for proppants, especially in downwell applications at higher temperatures (such as greater than 120 °C) and elevated pressures (such as in excess of 6000 psig), may be further improved by designing coatings that retain a high storage modulus at temperatures of up to at least 175 °C, which may be typically encountered during hydraulic fracturing of deep strata.
  • the coating may have a glass transition temperature greater than at least 140°C, e.g., may not realize a glass transition temperature at temperatures below 160°C, below 200°C, below 220°C, below 240°C, and/or below 250°C.
  • the resultant coating may not realize a glass transition temperature within a working temperature range typically encountered during hydraulic fracturing of deep strata.
  • the resultant coating may not realize a glass transition temperature within the upper and lower limits of the range from 25 °C to 250 °C. Accordingly, the coating may avoid a soft rubbery phase, even at high temperatures (e.g., near 200 °C and/or near 250 °C). For example, coatings that exhibit a glass transition temperature within the range of temperatures typically encountered during hydraulic fracturing of deep strata, will undergo a transition from a glassy to rubbery state and may separate from the proppant, resulting in failure.
  • any optional undercoat layer e.g., a polyurethane based layer may be formed first.
  • the amide based coating may be formed on (e.g., directly on) the article/proppant and/or the optional underlying undercoat.
  • solid core proppant particles e.g., which do not have a previously formed resin layer thereon
  • the solid core proppant particles may be heated to a temperature from 50 °C to 180 °C, e.g., to accelerate crosslinking reactions in the applied coating.
  • the pre -heat temperature of the solid core proppant particles may be less than the coating temperature for the coatings formed thereafter.
  • the coating temperate may be from 40 °C to 170 °C. In exemplary embodiments, the coating temperature is at least 85 °C and up to 170 °C.
  • the heated proppant particles may be sequentially blended (e.g., contacted) with the desired components for forming the one or more coatings, in the order desired.
  • the proppant particles may be blended with a formulation that includes one or more additives.
  • the proppant particles may be blended with a first isocyanate -reactive component in a mixer, and subsequently thereafter other components for forming the desired one or more coatings.
  • the proppant core particles may be blended with a liquid epoxy resin in the mixer.
  • a process of forming the one or more coatings may take less than 10 minutes, after the stage of pre-heating the proppant particles and up until right after the stage of stopping the mixer.
  • the mixer used for the coating process is not restricted.
  • the mixer may be selected from mixers known in the specific field.
  • a pug mill mixer or an agitation mixer can be used.
  • the mixer may be a drum mixer, a plate-type mixer, a tubular mixer, a trough mixer, or a conical mixer. Mixing may be carried out on a continuous or discontinuous basis. It is also possible to arrange several mixers in series or to coat the proppants in several runs in one mixer. In exemplary mixers it is possible to add components continuously to the heated proppants.
  • isocyanate component and the isocyanate-reactive component may be mixed with the proppant particles in a continuous mixer in one or more steps to make one or more layers of curable coatings.
  • any coating formed on the proppants may be applied in more than one layer.
  • the coating process may be repeated as necessary (e.g. 1-5 times, 2-4 times, and/or 2-3 times) to obtain the desired coating thickness.
  • the thicknesses of the respective coatings of the proppant may be adjusted.
  • the coated proppants may be used as having a relatively narrow range of proppant sizes or as a blended having proppants of other sizes and/or types.
  • the blend may include a mix of proppants having differing numbers of coating layers, so as to form a proppant blend having more than one range of size and/or type distribution.
  • the coated proppants may be treated with surface-active agents or auxiliaries, such as talcum powder or steatite (e.g., to enhance pourability).
  • the coated proppants may be exposed to a post-coating cure separate from the addition of the curative.
  • the post-coating cure may include the coated proppants being baked or heated for a period of time sufficient to substantially react at least substantially all of the available reactive components used to form the coatings. Such a post-coating cure may occur even if additional contact time with a catalyst is used after a first coating layer or between layers.
  • the post-coating cure step may be performed as a baking step at a temperature from 100 °C to 250 °C.
  • the post-coating cure may occur for a period of time from 10 minutes to 48 hours.
  • Amide based coatings (which include set in place coatings, spray coatings, powder coatings, and paints) may be used to protect surfaces.
  • the coating may be a permeable layer, such as a permeable liner.
  • 62/186,671 By permeable it is meant a liquid such as water, may penetrate into the coating. As discussed in U.S. Provisional Application No. 62/186,671, the
  • permeability of the layer may be determined by measuring the glass transition temperature (Tg) of the layer, before and after wetting the liner with water and correlating the Tg measurements to permeability.
  • Tg glass transition temperature
  • Another way to measure the liner permeability is using Electrochemical Impedance Spectroscopy (EIS), measures the dielectric properties of a medium as a function of frequency.
  • EIS Electrochemical Impedance Spectroscopy
  • liner permeability is by measuring the weight of the liner before and after exposing it to water at for instance 90 °C for at least 24 hours.
  • the coating process may involve a batch process, an intermittent process, or a continuous process using equipment well known to those skilled in the art.
  • techniques known in the art such as spraying, brushing (includes rolling), pouring in place, powder coatings, etc.
  • the coating composition may be applied form using equipment known to those skilled in the art.
  • the coating composition may be applied to large tanks and containers using spray equipment know to those skilled in the art.
  • any optional undercoat layer e.g., an epoxy or polyurethane based layer or primer
  • the amide based coating may be formed on (e.g., directly on) the base substrate and/or the optional underlying undercoat.
  • the components resin may be sprayed or brushed on to the base substrate at a same time.
  • the both the sulfide capturing agent and the polymer resin matrix are applied to the base substrate together (i.e., in a concurrent stage or step).
  • An exemplary a process of may include the following stages: (1) preparing a coating composition comprising at least one composition for components for forming the amide based coating; and (2) attaching, adhering or bonding the coating
  • Stage (2) may include processing the above coating composition to form a permeable liner on the base substrate by reacting/curing the composition of stage (1).
  • the coating composition may be applied at ambient conditions in the field. Thus, the application of the coating can be done e.g., by brush, by roller, by dipping, by spraying (air-less or air-assisted) using equipment known to those skilled in the art.
  • the coating may be applied in a dry film thickness of from 25 microns to 3000 microns. The coating cures at ambient conditions and may be in service in a period from 1 to 7 days.
  • the coating may be applied to the base substrate in a factory at ambient conditions and optionally baked at a higher temperature (e.g., greater than or equal to 40 °C, greater than or equal to 180 °C, greater than or equal to 100 °C, greater than or equal to 140 °C, and/or from 140 °C to 240 °C).
  • a higher temperature e.g., greater than or equal to 40 °C, greater than or equal to 180 °C, greater than or equal to 100 °C, greater than or equal to 140 °C, and/or from 140 °C to 240 °C).
  • the sulfide recovery coating is a one component of two components liquid coating material made from the above composition, whereas the liquid coating is useful for making a coating and/or liner for capturing contaminants.
  • the coating functions as a permeable layer for capturing contaminants, which coating is formed on the base substrate and may be made from the liquid coating material.
  • the coating is a permeable liner that functions as a permeable layer for capturing contaminants, which permeable liner may be adhered to the base substrate and may be made from the liquid coating material.
  • a coating composition in powder form may be dissolved in a solvent (such as xylene) and then be applied in liquid form.
  • the curable composition may be applied in liquid form direct to a metal substrate or a metal substrate coated with a primer (undercoat).
  • the curable composition can be also applied to composite and proppants applications.
  • Carboxylic Acid Copolymer 1 A poly-carboxylic acid copolymer having that is an anionic modified poly-alkylene glycol, which is radically grafted by acrylic acid, having an acid functionality of approximately 4.5, and an acid number ranging from 59.5 to 72.9 according to ASTM D-4662 (available as UCONTM EPML-483 from The Dow Chemical Company).
  • Carboxylic Acid Copolymer 2 A poly-carboxylic acid copolymer that has a nominal carboxylic functionality of 3 and is a lab- synthesized acid-terminated polyether prepared by first, in 1 liter 4 neck RB flask, charged IP 625 Polyol (available from The Dow Chemical
  • Citric Acid A polycarboxylic acid monomer that is citric acid which is available as 99% pure (available from Fisher Scientific).
  • Catalyst 1 A 1-methylimidazole catalyst (available from
  • Catalyst 2 A tertiary amine based catalyst that promotes the polyisocyanurate reaction, i.e., trimerization (available as Dabco® TMR from Air Products®).
  • Isocyanate A polymeric methylene diphenyl diisocyanate - also referred to as PMDI (available as PAPITM 27 from The Dow Chemical Company).
  • Adhesion Promoter An gamma-aminopropyltrimethoxysilane based adhesion promoter (available as SilquestTM A- 1100 from Momentive Performance Materials®).
  • Antiblocking additive produced from a
  • Zinc Oxide A powder that includes zinc oxide, believed to have an aerodynamic particle size from 50- 150 nm, (available as MKN-ZnO-050P from MKnano Canada).
  • Blends of a carboxylic acid, such as the Carboxylic Acid Copolymer 1 and/or 2, with the Citric Acid may be used to adjust the viscosity and acid number of the acid blend used in to for the amid based coating.
  • a carboxylic acid such as the Carboxylic Acid Copolymer 1 and/or 2
  • Citric Acid a carboxylic acid
  • Table 1 below, for various blends (each having a total weight of 100 wt%) of Carboxylic Acid Copolymer 1 with the Citric Acid, the measured viscosity and acid number is provided.
  • the viscosity and acid number of the blend may be varied by varying the ratio of acids used to form the amide coating.
  • ratios of 1:9 to 1:5 by weight of citric acid to the carboxylic acid such as Carboxylic Acid Copolymer 1 may be used to coat proppants.
  • the blends for the above and for the Examples below that include such blends are prepared as a lab sample using the following method. Firstly, the Citric Acid is added to Carboxylic Acid Copolymer lin a three-neck glass reactor at the desired ratio by weight.
  • the reactor is purged with nitrogen and the contents are stirred using a mechanical stirrer.
  • the temperature of the reaction mixture is raised to 100 °C using a heating mantle available from Glas- Col. After 3 hours at 100 °C, the contents are cooled and drained.
  • the citric acid and carboxylic acid formed as a pre-made blend prior to forming the amide based coating.
  • Viscosity measurements are performed on a TA Instruments AR-2000 rheometer with 40 mm cone-plate geometry and 54 ⁇ gap. Data ia collected with a constant temperature at 25 °C at a constant shear rate of 10 sec-1. Acid number is measured using ASTM D-4662, except methanol as the titration solvent versus ethanol/toluene is used by titration with potassium hydroxide.
  • the amide based coating is generally prepared by using a process in which from 600 to 750 grams of the Sand is heated to a temperature of up to 180 °C in an oven. Then, the heat Sand is introduced into a KitchenAid® mixer equipped with a heating jacket (configured for a temperature of about 70°C), to start a mixing process. During the above process, the heating jacket is maintained at 60% maximum voltage (maximum voltage is 120 volts, where the rated power is 425W and rated voltage is 240V for the heating jacket) and the mixer is set to medium speed (speed setting of 5 on based on settings from 1 to 10).
  • a mixture of the blend of the Carboxylic Acid Copolymer 1 or 2 and the Citric Acid is prepared, and then the blend is further mixed with the Catalyst 1 and/or 2 to form the blend with Catalyst.
  • the heated Sand is allowed to attain a temperature of 130-135°C.
  • the addition of the Isocyanate addition and addition of the blend with the Catalyst is performed.
  • a free-flowing product is obtained within a range of approximately 3 to 5 minutes.
  • the surface of the resin coated proppants is characterized by ATR-IR spectroscopy and scanning electron microscopy (SEM). Referring to FIG.
  • Comparative Example A has a coated structure that includes loss on ignition (LOI) -3% (as calculated based on the total quantity of resin added to sand), polyamide based coating, isocyanate index of 1.3, and cycle time of 4.5 minutes.
  • LOI loss on ignition
  • the sample is prepared using 750 grams of the Sand heated in an oven to 160 °C, then introduced into the KitchenAid® mixer. After temperature of the Sand reaches 125 °C, 0.6 mL of the Adhesion Promoter is added to the mixer.
  • Comparative Example B is Coolset® curable resin-coated sand available from Fairmount Santrol.
  • Working Examples 1 and 2 each have a coated structure that includes LOI -3.7%, polyamide based coating, isocyanate index of 1.0, and cycle time of 3 minutes. The samples are prepared using 600 grams of the Sand is heated in an oven to 160 °C, then introduced into the KitchenAid® mixer. After temperature of the Sand reaches 132 °C, 0.6 mL of the Adhesion Promoter is added to the mixer. Then, 15 seconds from start of addition of the Adhesion Promoter, 17.2 grams of premixed acid
  • Catalyst 1 (0.7 grams) is added simultaneously with 6.0 grams of Isocyanate over a period of 1.25 minutes. The mixer is stopped after 1.5 minutes. Material is emptied onto a tray and allowed to cool.
  • Working Examples 3 and 4 each have a coated structure that includes LOI ⁇ 3 %, polyamide based coating, isocyanate index of 1.0, and cycle time of 3 minutes.
  • the samples are prepared using 750 grams of the Sand is heated in an oven to 160 °C, then introduced into the KitchenAid® mixer. After temperature of the Sand reaches 135 °C, 0.6 mL of the Adhesion Promoter is added to the mixer. Then, 15 seconds from start of addition of the Adhesion Promoter, 17.2 grams of premixed acid
  • Catalyst 1 (0.7 grams) is added simultaneously with 6.0 grams of Isocyanate over a period of 1.25 minutes. The mixer is stopped after 1.5 minutes. Material is emptied onto a tray and allowed to cool.
  • Working Example 5 has a coated structure that includes LOI ⁇ 3 %, polyamide based coating, isocyanate index of 1.25, and cycle time of 3 minutes.
  • the sample is prepared using 750 grams of the Sand is heated in an oven to 160 °C, then introduced into the KitchenAid® mixer. After temperature of the Sand reaches 135 °C, 0.6 mL of the Adhesion Promoter is added to the mixer.
  • the sample is prepared using 750 grams of the Sand is heated in an oven to 160 °C, then introduced into the KitchenAid® mixer. After temperature of the Sand reaches 135 °C, 0.6 mL of the Adhesion Promoter is added to the mixer. Then, 15 seconds from start of addition of the Adhesion Promoter, 16.6 grams premixed acid Carboxylic Acid Copolymer 1 / Citric Acid at a ratio of 9: 1 (15.7 grams) with Catalyst 1 (0.7 grams) and Catalyst 2 (0.2 grams) is added simultaneously with 6.8 grams of Isocyanate over a period of 1.25 minutes. The mixer is stopped after 1.5 minutes. Material is emptied onto a tray and allowed to cool.
  • Working Example 7 has a coated structure that includes LOI ⁇ 3 %, polyamide based coating, isocyanate index of 1.25, and cycle time of 3 minutes.
  • the sample is prepared using 750 grams of the Sand is heated in an oven to 160 °C, then introduced into the KitchenAid® mixer. After temperature of the Sand reaches 135 °C, 0.6 mL of the Adhesion Promoter is added to the mixer. Then, 15 seconds from start of addition of the Adhesion Promoter, 15.4 grams of premixed acid Carboxylic Acid Copolymer 2 (14.6 grams) with Catalyst 1 (0.8 grams) is added simultaneously with 7.9 grams of Isocyanate over a period of 1.25 minutes. The mixer was stopped after 1.5 seconds. Material is emptied onto a tray and allowed to cool.
  • Working Example 8 has a coated structure that includes LOI ⁇ 3 %, polyamide based coating, isocyanate index of 2, and cycle time of 3 minutes.
  • the sample is prepared using 750 grams of the Sand is heated in an oven to 160 °C, then introduced into the KitchenAid® mixer. After temperature of the Sand reaches 135 °C, 0.6 mL of the Adhesion Promoter is added to the mixer. Then, 15 seconds from start of addition of the Adhesion Promoter, 13.0 grams of premixed acid Carboxylic Acid Copolymer 2 (12 grams) with Catalyst 1 (0.8 grams) and Catalyst 2 (0.2 grams) are added simultaneously with 10.5 grams of Isocyanate over a period of 1.25 minutes. The mixer is stopped after 1.5 minutes. Material is emptied onto a tray and allowed to cool.
  • Working Example 9 has a coated structure that includes LOI ⁇ 3 %, polyamide based coating, isocyanate index of 1.25, and cycle time of 4 minutes.
  • the sample is prepared using 750 grams of the Sand is heated in an oven to 160 °C, then introduced into the KitchenAid® mixer. After temperature of the Sand reaches 135 °C, 0.6 mL of the Adhesion Promoter is added to the mixer.
  • Working Example 10 has a coated structure that includes LOI ⁇ 3 %, polyamide based coating, isocyanate index of 2, and cycle time of 4 minutes.
  • the sample is prepared using 750 grams of the Sand is heated in an oven to 160 °C, then introduced into the KitchenAid® mixer. After the temperature of the Sand reaches 135 °C, 0.6 mL of the Adhesion Promoter is added to the mixer. Then, 15 seconds from start of addition of the Adhesion Promoter, 13.0 grams of premixed acid Carboxylic Acid Copolymer 2 (12.0 grams) with Catalyst 1 (0.8 grams) and Catalyst 2 (0.2 grams) is added simultaneously with 10.5 grams of Isocyanate over a period of 1.25 minutes. Antiblock (5.0 grams) is sprinkled over a period of 15 seconds while the Sand is being mixing. The mixer is stopped after 45 seconds. Material is emptied onto a tray and allowed to cool.
  • Working Example 11 has a coated structure that includes LOI ⁇ 3 %, polyamide based coating, isocyanate index of 1, and cycle time of 4.5 minutes.
  • the sample is prepared using 750 grams of the Sand is heated in an oven to 160 °C, then introduced into the KitchenAid® mixer. After temperature of the Sand reaches 135 °C, 0.6 mL of the Adhesion Promoter is added to the mixture.
  • Unconfined compressive strength is measured using an MTS Insight electromechanical compression tester. More specifically, for forming the "plug", the customized molds (3 parts - 1 inch inner diameter, 1 3/8" outer diameter) are obtained from Collin Instruments, the pressure is controlled using a hot press (— ), and the temperature is controlled using a heat tape from (Brisk Heat). Solid wax is used around the sides of the molds to provide lubrication aiding in the removal of the plugs from the mold. Typically, 25 - 30 grams of coated sample is poured into the mold after locking the mold at the bottom (sealing the mold at the bottom using Teflon tape), heat tape is wrapped around the mold.
  • UCS Unconfined compressive strength
  • Dry compressive strength is measured to evaluate the flowability of Working Examples 9 and 10, which include the anti-blocking agent.
  • Example 11 a process involving simultaneous injection of polyacid and polyisocyanate onto a rapidly stirred mixture of hot sand particles is utilized to prepare the samples.
  • Working Example 11 shows 100% capture of H2S in 1 h at 70 °C.
  • Table 4 [0081] 3 ⁇ 4S capture is measured by gas chromatography and the percent capture is based on the vapor-liquid equilibrium assumption.
  • the initial head space concentration of 3 ⁇ 4S is 3133 ppmv.
  • the media used for the test is deionized water and the proppant concentration is 20 wt%.
  • Hydrogen sulfide capture studies are performed, by using 2.0 grams of each sample, which is weighted into a 22-mL headspace GC vial with a stir bar. Deionized water (10 mL) is then added into each vial and sealed with a PTEF lined silicon crimp cap. Hydrogen sulfide gas (1.5 mL, STP equivalent to 2.28 mg) is injected into the headspace of each vial.
  • the vials are then heated at 70°C in an aluminum heating block on top of a stirring hot plate for 1 hour, after which the vials are cooled and the 3 ⁇ 4S concentrations in the headspace of the vials are analyzed by headspace gas chromatography. Each sample is prepared in duplicate.

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Abstract

Cette invention concerne un article revêtu comprenant un article, et un ou plusieurs revêtements à base d'amide sur une surface extérieure de la particule d'agent de soutènement, le revêtement à base d'amide comprenant le produit de réaction d'un composant isocyanate qui contient au moins un isocyanate et d'un composant acide carboxylique constitué d'un ou de plusieurs acides polycarboxyliques.
PCT/US2017/034275 2016-06-08 2017-05-24 Revêtement à base d'amide WO2017213855A1 (fr)

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BR112018075389A BR112018075389A2 (pt) 2016-06-08 2017-05-24 revestimento à base de amida
CA3027004A CA3027004A1 (fr) 2016-06-08 2017-05-24 Revetement a base d'amide
CN201780035150.8A CN109348721A (zh) 2016-06-08 2017-05-24 酰胺类涂层

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